Digital Transformation Lessons Learned from Failures in an Urban Hospital Network

A bstract This paper examines the complex challenges of digital transformation in a healthcare organization that has relied on an outdated, mainframe-based system from the 1990s. Despite expanding its services into modern care, the failure to modernize core digital infrastructure has created a misalignment between its legacy technology and current operational needs. The crisis stems from interconnected issues, including a passive strategic posture that prioritized short-term cost containment, inadequate risk management, and a lack of leadership readiness. These compounded failures have hindered the organization’s ability to adapt and align with the demands of contemporary healthcare, underscoring the critical need for comprehensive change management that addresses both structural and cultural elements of the organization.